[(E)-4-({(R)-2-Benzyloxy-1-[methyl-((R)-1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-ethyl}-methyl-carbamoyl)-1,1-dimethyl-but-3-enyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(E)-4-({(R)-2-Benzyloxy-1-[methyl-((R)-1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-ethyl}-methyl-carbamoyl)-1,1-dimethyl-but-3-enyl]-carbamic acid tert-butyl ester
• CAS No.: 193085-41-5
• Molecular Formula: C₃₄H₄₈N₄O₆
• Molecular Weight: 608.778
• Mol file: 193085-41-5.mol

Synonyms:

Chemical Property of [(E)-4-({(R)-2-Benzyloxy-1-[methyl-((R)-1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-ethyl}-methyl-carbamoyl)-1,1-dimethyl-but-3-enyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(E)-4-({(R)-2-Benzyloxy-1-[methyl-((R)-1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-ethyl}-methyl-carbamoyl)-1,1-dimethyl-but-3-enyl]-carbamic acid tert-butyl ester

There total 9 articles about [(E)-4-({(R)-2-Benzyloxy-1-[methyl-((R)-1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-ethyl}-methyl-carbamoyl)-1,1-dimethyl-but-3-enyl]-carbamic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-tert-butoxycarbonyl-N-methyl-D-phenylalanine (37553-65-4,64263-83-8,85466-66-6) → [(E)-4-({(R)-2-Benzyloxy-1-[methyl-((R)-1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-ethyl}-methyl-carbamoyl)-1,1-dimethyl-but-3-enyl]-carbamic acid tert-butyl ester (193085-41-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 1-hydroxybenzotriazole hydrate, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, MeOH, overnight

2: 89 percent / TFA / CH₂Cl₂ / 1 h

3: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH₂Cl₂, DMF, 15 min, 2.) CH₂Cl₂, DMF, overnight

4: TFA / CH₂Cl₂ / 0.17 h

5: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH₂Cl₂, DMF, 15 min, 2.) CH₂Cl₂, DMF, overnight

With 1-hydroxy-7-aza-benzotriazole; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm980197u

Reference yield:

3-[(tert-butoxycarbonyl)amino]-3-methylbutanoic acid (129765-95-3) → [(E)-4-({(R)-2-Benzyloxy-1-[methyl-((R)-1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-ethyl}-methyl-carbamoyl)-1,1-dimethyl-but-3-enyl]-carbamic acid tert-butyl ester (193085-41-5)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / tetrahydrofuran / 0.67 h / 0 °C

2: LiBH₄ / tetrahydrofuran / 6 h / 0 - 20 °C

3: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -78 deg C to RT

4: 1.) t-BuOK / 1.) THF, RT, 40 min, 2.) THF, RT, 75 min

5: aq. LiOH / dioxane / 16 h / Ambient temperature

6: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH₂Cl₂, DMF, 15 min, 2.) CH₂Cl₂, DMF, overnight

With lithium hydroxide; lithium borohydride; 1-hydroxy-7-aza-benzotriazole; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm980197u

Reference yield:

(1,1-dimethyl-3-oxo-propyl)-carbamic acid tert-butyl ester (181646-38-8) → [(E)-4-({(R)-2-Benzyloxy-1-[methyl-((R)-1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-ethyl}-methyl-carbamoyl)-1,1-dimethyl-but-3-enyl]-carbamic acid tert-butyl ester (193085-41-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) t-BuOK / 1.) THF, RT, 40 min, 2.) THF, RT, 75 min

2: aq. LiOH / dioxane / 16 h / Ambient temperature

3: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH₂Cl₂, DMF, 15 min, 2.) CH₂Cl₂, DMF, overnight

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; potassium tert-butylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane;

DOI:10.1021/jm980197u

upstream raw materials:

N-tert-butoxycarbonyl-N-methyl-D-phenylalanine

3-[(tert-butoxycarbonyl)amino]-3-methylbutanoic acid

(1,1-dimethyl-3-oxo-propyl)-carbamic acid tert-butyl ester

tert-butyl (3-hydroxy-1,1-dimethyl-propyl)-carbamate